Sinteza konjugata ferocena i celobioze

master's thesis

• Title (english): Synthesis of ferrocene and cellobiose conjugates
• Author: Adriana Lipovčić
• Mentor: Đani Škalamera (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Aleksandra Maršavelski (član povjerenstva)
• Committee member: Jana Pisk (član povjerenstva)
• Committee member: Željka Car (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2024-01-19, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U sklopu ovog diplomskog rada priređeni su konjugati ferocena i celobioze, čija je svrha proučavanje potencijalnog prijenosa kiralnosti sa šećernog dijela molekule na ferocensku jezgru putem supramolekulskih interakcija. Inspiracija za sintezu navedenih spojeva proizašla je iz klase ferocenskih peptida koji posjeduju svojstvo helikalne kiralnosti, koje potječe iz stabilizacije konformera putem intramolekuslkih vodikovih veza. Ferocenski peptidi našli su primjenu u dizajnu stereoselektivnih katalizatora i supramolekulskih sustava, ali do sada nisu istraženi njihovi analozi koji sadrže saharidne jedinice umjesto aminokiselinskih. Sinteza je započeta od celobioza-oktaacetata kojem je dodana alkilna poveznica metodom izravne glikozilacije uz brometanol. Bromid je zatim supstituiran azidom koji je reduciran do amino skupine. U standardnim uvjetima priprave amidne veze, amino skupina kondenzirana je s karboksilnom skupinom ferocenske(bis)karboksilne kiseline, dajući zaštićene konačne spojeve kao produkte, kojima su u posljednjem sintetskom koraku uklonjene acetatne zaštitne skupine. Konačni produkti i međuprodukti sinteze okarakterizirani su spektroskopskim tehnikama (NMR, IR).

Abstract (english)

As part of this thesis, conjugates of ferrocene and cellobiose were prepared, aimed at studying the potential transfer of chirality from the sugar part of the molecule to the ferrocene core through supramolecular interactions. The inspiration for the synthesis of these compounds came from the class of ferrocene peptides, which possess the property of helical chirality, originating from the stabilization of conformers through intramolecular hydrogen bonds. Ferrocene peptides have found applications in the design of stereoselective catalysts and supramolecular systems, but their analogs containing saccharide units instead of amino acids have not yet been explored. The synthesis began with cellobiose octaacetate to which an alkyl linker was added by the method of direct glycosylation with bromoethanol. The bromide was then substituted with azide, which was reduced to an amino group. Under standard conditions for the preparation of amide bonds, the amino group was condensed with the carboxyl group of ferrocene(bis)carboxylic acid, yielding protected final compounds as products, from which acetate protective groups were removed in the final synthetic step. The final products and intermediates of the synthesis were characterized by spectroscopic techniques (NMR, IR).

• Keywords: celobioza; ferocenski peptidi; glikozilacija; helikalna kiralnost; intramolekulske vodikove veze
• Keywords (english): cellobiose; ferrocene peptides; glycosylation; helical chirality; intramolecular hydrogen bonds
• Language: croatian
• URN:NBN: urn:nbn:hr:217:946301
• Study programme: Title: Graduate university studies in chemistry; specializations in: Graduate university studies in chemistry; Course: Graduate university studies in chemistry; Study programme type: university; Study level: graduate; Academic / professional title: sveučilišni/a magistar/magistra kemije (sveučilišni/a magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2026-01-19
• Created on: 2024-01-26 09:24:09